I wanted to re-post some links I found in this thread from the tribe group that are non-operational. I took over the moderation of that group and renamed the group Pegging 101. There are a some good threads there. Although I must say - this group is far more active and lively than they have found the courage to be as yet.... :-)Tribes - Pegging 101

Thanks for the Tribes links -- some interesting stuff in there. Not only are those threads less active than the related ones here, the groups don't have much cohesion. Your website is better, having cohesion, focus, information and entertaining stories (excellent erotic writing, BTW).

I'd be happy to! Thanks for the invitation. (and for the second, MarkM)

Please be aware that as I mentioned before, while there is certainly never any expectation or obligation to engage in pegging in any particular manner (esp. like porn portrays it) and a couple can practice it as simply one more way to experience intimacy and pleasure together...my own particular leanings are dominant with a touch of light S/M thrown into the mix...but always consensual. And I most often write to satisfy my leanings. Definitely don't want to offend anyone if that's not your cup o' tea.

I'm glad you enjoyed them. People's preferences are so varied that I probably cater to a small slice of erotica readers.However I did notice that this definitely kicked up the traffic significantly coming from this website - according to my Google Analytics...and y'all spent some time there, too. Couple of new memberships as well! Thanks guys.All the best,Ruby

Thank you indeed Ruby.I have listened to you reading your stories.As you say my kinks are your kinks.I have not been very active on forum or chat lately due to domestic problems.I hope this will change at the end of the month and that I will have time to resume my scribbles and Rectumland adventures.

I thought you, and some guys here might be interested in what I'd do differently if I were a would-be beginner at pegging, knowing what I know now, three months down the road.

First, doing what I did, buying a harness-free double dildo (FunFactory Share) and just springing it on your lady, "Here, let's try this!" is not a great idea (duh), even though she did play along. Harness-free designs like Share and Feeldoe are problematic for most women in terms of holding on with PC muscles alone. That sets up a failure mode, which requires buying a harness to fix a problem you don't need at the start. (Save the harness-free concept for when you're both already enjoying pegging.) Here's a better approach for beginning:

Ask her, if you don't know already, if she is comfortable with the idea of sex toys. If she's not, you'll have to get her to that point before proceeding.

Regarding her preference in sex toys, does she get off on clitoral stimulation by itself? Clitoral stim with a dildo inserted? Dildo by itself? Vibrating or not? The answers to those questions will guide the two of you in selecting her part of the pegging hardware.

If she doesn't already own the vibe and/or dildo for her side of the rig, buy that and let her play with it. Ideally, you should shop online, together.

Buy a high-quality harness that supports her preference on her side. For example, could be a harness that holds a clitoral butterfly vibe/bullet or a harness that holds her favorite type of dildo, or both. The Annie-O harness by Outlaw Leather can do any combo. The SpareParts Joque offers fewer options.

Buy a dildo for your side of the rig and practice solo with it. If it's at all uncomfortable, get another.

Warm up for an hour with your favorite Aneros (Vice, for me).

Put the rig together and try it out. I hope it's good for both of you.

You know, Dave - I am so glad you mentioned this because this is an issue I run across often. Thanks for this.

When men are first getting interested in pegging many of them are quite concerned about wanting their partner to have pleasure as well and they think that the only way to do that is with one of the double-ended dildos like the feeldoe, realdoe, share, etc. They do indeed look really sexy - that's for certain. I try to warn people that they have their issues - exactly like you mentioned (vaginal muscles cannot compete with anal sphincters) but still many buy them. I firmly believe that it is an advanced toy, as you say, and from now on I intend to tell people that more strongly. I appreciate you sharing your story with us - it helps to be able to hear the feedback from having chosen that as a first toy. Again - some people love them - but those folks are in the minority.

Double-ended dildos such as those are not the only way for a woman to have pleasure! there are harnesses with clit vibes, dildos with vibes in the base and harnesses with the ability to have a single flared-base dildo in both of you. Depending on how the woman gets off - any of these can be a great choice....

I go into a fair amount of detail about harness and dildo choices here. Happy shopping!

So I finally broke down and decided I want to be pegged so I checked online for prostate massages in my area (not the USA anymore) and found a sensual massage therapist (more of a dominatrix-lite though) who specializes in prostate play with either a finger or strapon. It was also surprisingly cheap, about USD $110 for the hour.

So I get to my appointment and explain that I've never been fucked by either a strapon or dick before, but I would like to pegged for almost the entire hour and she seemed surprised that a relative newbie would want to do it for that long, but reluctantly agreed. She started off with a sensual massage for about 10 minutes, I was on my stomach and she was on top of caressing my whole rear, but not yet putting a finger in there. Let me say, this felt absolutely incredible and by the end I couldn't keep my arms still b/c even they were tingling so much.

Next, she tells me to lay on my back and I agreed to light restraint so she puts my hands on top of my head and ties them. She does a bit more sensual massaging for about 5 minutes including this thing where she put light pressure on my perineum and just kept kind of pumping it, kind of like someone might do on your chest when giving CPR, if that makes sense. Anyway, that felt incredible and I think I may have been able to bring myself to at least a mini-O had she kept doing it.

Next, she starts working a finger into my anus, I was a little let down b/c it obviously felt good, but after the buildup from the previous 15 minutes I thought it would send pangs of pleasure all over. She worked with one finger for a little while and kind of massaged around my frontside with her other hand. I instructed her not to stroke my cock until the very end so I could focus on prostate sensations, so she obliged, but would lightly touch my cock every now and then which was great.

So she finally gets to the pegging and she told me she picked her smallest dildo it was probably only a little girthier than the Progasm (which I normally use) and was flared a bit at the end towards the prostate. I'm not really sure though at which point she went from a finger to the strapon so maybe it wasn't that big. Anyway, she started pounding away slowly, gradually pick up the pace, and me slightly adjusting my hips so she hit the right spots and she followed my cues nicely. This went on for awhile until she really started pounding away and it felt like she was hitting my prostate and it felt pretty good, but unfortunately I couldn't really build up enough feeling around the prostate to approach any kind of prostate O. If I had to guess I would say it was partly the new-ness of the sensation of being fucked (which I'm not used to), partly b/c there's a bit of a time constraint b/c prostate orgasms can take some time to build up to, and partly b/c I had never done anything like this before and I was incredibly anxious and excited and maybe couldn't calm down enough.

Overall I would rate the session a 6 out of 10, parts of it were incredible and mind-blowing, but surprisingly they all pretty much occurred while I wasn't being penetrated by either a finger or strapon. I was a bit let down by the actual pegging, don't get me wrong it felt good, but I was hoping it could bring me to the verge of prostate O's or beyond, but I didn't really feel like I got very close. I think I will definitely do this again, probably in a week or 2, but I will have to change things up a bit. I think I will ask her to do the sensual massage type warmup for 15-20 minutes, then have her manually stimulate my prostate with a finger or two while keeping pressure on my perineum. I'm hoping this setup might be more conducive to a mini-O. Towards the end I will have her use a slightly larger dildo, possibly with a vibrator b/c I love my Vice too and the vibrations really send me over the edge.

Towards the end of the session she starts stroking me for the big finish, but oddly I had trouble getting an erection. Usually during my Aneros sessions I get rock hard erections that I can keep for awhile, but outside of the first 10 minutes with the sensual massage, and the last 2 minutes right before I ejaculated, I couldn't really get an erection, which was a bit disappointing and surprising. She kind of had to stop thrusting the strapon and focus more on getting me off, and when I finally did, it was a decent orgasm, but nothing mind blowing. I knew I was actually a bit over my hour time limit, so I couldn't really focus on the sensations of my prostate while cumming, which usually intensifies it greatly.

I hope this wasn't too long and I'd appreciate any comments and feedback. Mainly I'm wondering if this type of stuff is pretty normal for your first time being pegged (i.e. not being able to prostate O from it, not being able to stay hard, etc.) and I'm also wondering if anyone has any suggestions on what I should try to do next time to possibly heighten the pleasure. Maybe the hour long format with someone who you don't feel an emotional attachment to isn't conducive to bringing about an orgasm. Hopefully next time I'll be a bit more relaxed, a bit more used to the sensations involved, and I'll know what I like a bit more and maybe turn the session from a 6/10 to a 9//10.

Getting a prostate orgasm during pegging took me more than a few tries. Now, I get multiples. Like with the Vice+vibe, the key is to relax while being fucked. That was very difficult with the heavy vibes from the Vice and is even more difficult when banged by a dildo that's considerably larger.

Another thing that helped me get there was to ride on top, cowboy-style. That allows you to have precise control of depth, angle, rhythm and speed. I think being in control helps maintain an erection as well. While I agree that an erotic massage is a good warm-up, I find that 30 minutes with the Vice+vibe before pegging is essential.

ten_s, that makes a lot of sense about relaxing, I kinda figured that was a large part of it b/c I was so anxious and nervous about the whole ordeal I couldn't even really sleep the night before the appointment. Probably not really conducive to orgasmic results. Hopefully next time I'll be able to relax more. I can relate to what you said about the Vice+Vibe, that took me many tries as well, but now produces amazing results most sessions. With your last comment in paragraph 2 are you suggesting that it might be beneficial to have a mini session with the Vice+Vibe right before leaving for my session as a warm-up?

I'm not sure if I'm bold enough to try riding on top, or if she'd even allow it, maybe a couple more sessions down the road. Usually during my Aneros sessions I get the best results lying on my stomach, would it work very well if I did this while being pegged or is too hard to get a good angle on the prostate that way? Also, what do you think works best when she's having her way with you - long, slow thrusts, rapid thrusts, maybe holding the strap-on in deep and having her slowly rotate or grind her hips? Finally, do you think having a vibrating strapon vs. non-vibrating makes a huge difference? I'm thinking about asking if she has a vibrating strapon. Sorry if that's a lot of questions, but you're the master and I want to make the most of this next session.

Thanks for asking, but I'm no "Master" at pegging. My wife and I have been at it only 4 months. We're still learning.

The second best position for me after cowboy is reverse missionary; me laying on my back, legs up, wife on top. That allows the wife easy access to my dick. In that position I like a few slow and deep followed by fast and shallow thrusts, repeat.

On the other hand, she prefers fucking me when I'm face-down, flat on the bed, legs together. She can get a good angle on my prostate but sometimes gets too energetic. The short high frequency jiggling thrusts work best in that position. It's similar to what you see in the video linked below in terms of speed and rhythm, but with more depth (our dildo is 3X bigger). The corkscrew rotation thing is kind of hit or miss. I think the depth has to be exactly spot-on for it to feel good.

All of our dildos are doubles, with vibes. The vibes help, especially since they remind me of the Vice.

Finally, yes, have a mini-session for 15 or 30 minutes with the Vice before going to your pegging appointment. It really warms everything up nicely.

Hey Dave - I finally changed the section in my FAQs that talks about double-ended dildos:

A word about double-ended dildos like the Share and the Feeldoe...most couples find that these cannot be used without a harness, no matter how sexy that may be to envision. I would like to emphasize that they are on the advanced end of pegging toys for the majority of people. Some couples love them, but most use a harness as well and they are indeed in the minority. The difficulties arise from a) vaginal muscles being no match against the anal sphincter so they are difficult for most women to even keep in, b) the insertion point is the only point of balance as opposed to a nice snug two strap harness which will let you push up down and sideways and c) imagine dealing with all that when you are just learning how to fuck someone else! Not recommended for beginners.

Rando - Thanks so much for the in-depth (pun intended) report! Having a prostate O the first time you are pegged is not the norm. There are no studies (yet!) but here is my guess from observation and information gathering. I think the percentage of men who orgasm easily from pegging in the beginning are about the same as the percentage of women who orgasm from G-spot stimulation easily - about 25 - 30%. There are threads that talk about orgasms from pegging on FetLife and you can find all different responses; men who have to have cock stimulation to orgasm, men who can have a prostate O sometimes and men who barely need to be entered to orgasm.

I have also encountered men who after being pegged for a long time get kind of overstimulated and can't get hard or orgasm until the anal stimulation reduces or stops. And as far as the erection reaction to pegging, there is no hard and fast rule. There are men who can't get erect at all, men whose erections come and go and men who stay hard the entire time. I do not know how this compares to erections while using the Aneros toys.

As an aside, I really wish there were prostate massage/dom lite practitioners openly available in the US, as I get asked for referrals all the time.

Thanks for the info Ruby! I was all set for my 2nd visit last Tuesday, but alas she canceled due to an illness, so I'll have to wait until next Tuesday.

Usually when using the prostate I'd say I'm hard maybe 40-50% of the time, while having a Super O, I really couldn't say b/c I don't really care, lol, but then towards the end of a session when I want a traditional O, I find it's easy to get hard and stay hard for over 30 minutes (if I choose). That's why I was a little bit surprised at my inability to get hard towards the end of my first "massage therapy" session even when cock stimulation began.

One thing that I think played a huge factor is that the night before session 1 I really could not sleep at all and was just really anxious about the whole ordeal. The night before what was supposed to be session 2 (keep in mind I didn't know it'd be canceled yet) I was still looking forward to the session, but got a good night's rest. So I am thinking being so amped up about the whole ordeal may have made it even more difficult to get a Super O and then get hard throughout the session. We'll see next time, I'm so excited and I'm gonna do 90 minutes instead of 60, and already have a better plan based on what felt like it worked the first time. I'm really hoping she has a vibrating strapon as well.

Okay, I am working slighty out of order on all of the posts that I need to finish, but I think K5 might explode if I don’t get this posted. As Deviant has already told everyone, I had a huge fantasy to use a strap-on with him. It is just so empowering to think about me on top, to think about me being the one in complete control.

I used to have a huge problem with fantasies. It’s not that I had anything against them, it’s just that I rarely had them. When I did have them, I never told anyone about them. I still know that I don’t have as many as some people, but at least I fantasize now. So, I had thought about pegging Deviant in the ass for a while, and one night in bed, he asked me what my craziest fantasy was… that’s the one I told him about!

When my strap-on arrived in the mail, I sent Deviant a message right away telling him. He immediately wrote back saying “is that a subtle hint that you want to fuck me in the ass tonight?”

Maybe…

Later that night, I noticed that Deviant had poured himself a drink. This isn’t normal for him, so I knew that he was nervous about it. I was also a little nervous, but I was also really excited. When he went to get in the shower, I went to open everything up and get it ready. I had the harness on and when he came out of the shower, but the dildo hadn’t been cleaned yet, so it wasn’t attached yet.

He told me to get everything ready, and come let him know when I was. After everything was clean and ready, I went to go get him. We both giggled about the purple cock that was between my legs for a few minutes.

I decided that he deserved to get a blow job to start things off. I gave my best efforts, and it was obvious that Deviant liked what was happening. He was rock hard and I could taste the cum that was leaking from the end of his cock. He looked me in the eyes after a few minutes and told me that if I was ready, so was he.

I was a little shy about what was about to happen, and luckily, Deviant noticed. He asked me how I wanted him. That was all of the encouragement that I needed!

I told him to bend over the bed, and he listened to me. I got the lube out and ready while he bent over the bed. I positioned myself behind him and started to slowly enter him. I needed his help to guide it in since I couldn’t really feel what was going on.

After a short break, we were able to get the dildo all the way in. I immediately went into “I’M FUCKING HIM IN THE ASS” mode. I grabbed hold and started thrusting. Apparently I wasn’t very gentle, and he had to ask me to slow down once. I had 2 problems with this position: 1) I couldn’t feel how far out I was pulling, so a few times I pulled all the way out and 2) it was really hard to give a reach around! (but I did try)

We decided that a different position might work better, so I laid flat on the bed, and Deviant lowered himself onto my purple cock sideways. This was much better for the reach around. I was able to jack him off while he was getting nailed.

It was so fucking hot to hear him moan while this was all happening. I know that he was doing this for my fantasy, but, what a feeling to know that he was enjoying it, too.

Next position: missionary-like. Deviant flat on his back while I thrusted into him. I think we both liked this on the best. I was able to get some real thrusting, and I could hear him moan and see the pre-cum that was covering his stomach and chest. I really got into it at this point. I was really hoping that I would make him cum while I was nailing him. I could also feel myself getting more and more excited. As I thrusted, I could feel my clit swelling. With every shove and moan that came from Deviant, I got more and more excited.

There is nothing like the power and control that I felt while we were doing this. I have played Mistress before, but this was different. This was complete and total control. It was such a different feeling for me, and I was having a blast.

I started having troubles with the dildo slipping out again, so we decided to call it quits with pegging.

At this point, I wanted to make him cum. I wanted him to get off. I wanted to taste his cum. I sucked and licked with all of my might. I could feel his cock, so hard, sliding between my lips. I could taste him in the back of my throat.

When he came, it was awesome. There was such a load, and I loved it. Afterwards, we talked about it. I wanted to make sure that he had a good time. I also wanted to make sure that he understood how excited I was that he did this for me. Granted, I doubt he could have not known with the smile that was spread across my face.

This was such a wonderful evening. I had always thought about it. I had always wanted to know what it would be like to be able to do it. And now, here I am, with another fantasy off the list! Deviant made that happen. and… IT WAS HOT!

A wonderful message sent to me through my website. Sharing from the female POV is rare - I received her permission to post this.

Six months ago my fiancée, then boyfriend of two and a half years, told me he had tried anal play during masturbation and was interested in exploring this together. At first I was mildly upset/offended. Hadn't I been a good enough lover? Was he bi-because he certainly isn't gay. Most importantly we had been fucking for two years and he never mentioned it, although he had mentioned an interest in giving anal pleasure. I began to feel ill-equipped to please him, compared to a toned man with a raging hard cock.

Since then he has shared all of his sexual experiences with me, and I have learned that no, my future husband is not gay. Rather he is a heterosexual male who really enjoys having his ass fucked by a woman, and a prostate massage in tandem with being blown.

The best part is...I LOVE it. Seeing my glistening purple Share dildo right before I penetrate him gets me so hot, and I love hearing him moan as he gives me his ass and totally submits all thought.

There is something so erotic about being fucked and submitting as I am being penetrated. To simply feel, and not think. I am so happy to bring that same pleasure I experience to the best lover I have ever known and get to spend a lifetime in the sack with. Since we have started pegging, it has become a normal aspect to our sex life.

I am still coming to terms with accepting that I like to fuck and make sweet love to his ass, but I am coming to accept it. I enjoy taking his ass, and desire to be inside him almost as much as I long for his tongue on my clit when he is at work.

What a delightful message! It's so wonderful to read about a woman who has a passion for delivering anal pleasure. I love how she likens it to her own experience of being penetrated as well. Thanks for sharing Ruby.

This part definitely struck a chord with me: "There is something so erotic about being fucked and submitting as I am being penetrated. To simply feel, and not think."

It's so nice to just give up complete control sometimes and be able to "sit back" and just enjoy the ride.

I'm wondering if anyone else feels the same way, but one of the reasons I love prostate play (whether by myself of being pegged) is that I can just experience endless pleasure and can decide myself when it ends. When you are penetrating a female, you can't quite let loose fully b/c at least in the back of my mind I have to temper my pleasure a bit lest I ejaculate and then it immediately ends. So you enjoy the experience, but you don't want it to end, so you can't experience too much,or it might end, it's like a constant balancing act.

And more to the subject of pegging or anal play in general, is it best to let it be known very early in a budding relationship? It seems like it's a bit more of a shock to a female to learn about a male's desire to be pegged if they've just been having traditional sex for a year+, but maybe if you introduce it very early in a relationship, it can lead to much more favorable outcomes. I will also throw out there that I'm in my mid-20s and about to embark on a new relationship (yet to have sex), but it's gotten to the point where if a potential partner is unwilling to take part in pegging, that it is basically a dealbreaker, b/c I enjoy it so much. :)

[QUOTE=Rando;101548]This part definitely struck a chord with me: "There is something so erotic about being fucked and submitting as I am being penetrated. To simply feel, and not think."

It's so nice to just give up complete control sometimes and be able to "sit back" and just enjoy the ride.

I'm wondering if anyone else feels the same way, but one of the reasons I love prostate play (whether by myself of being pegged) is that I can just experience endless pleasure and can decide myself when it ends. When you are penetrating a female, you can't quite let loose fully b/c at least in the back of my mind I have to temper my pleasure a bit lest I ejaculate and then it immediately ends. So you enjoy the experience, but you don't want it to end, so you can't experience too much,or it might end, it's like a constant balancing act.

And more to the subject of pegging or anal play in general, is it best to let it be known very early in a budding relationship? It seems like it's a bit more of a shock to a female to learn about a male's desire to be pegged if they've just been having traditional sex for a year+, but maybe if you introduce it very early in a relationship, it can lead to much more favorable outcomes. I will also throw out there that I'm in my mid-20s and about to embark on a new relationship (yet to have sex), but it's gotten to the point where if a potential partner is unwilling to take part in pegging, that it is basically a dealbreaker, b/c I enjoy it so much. :)

There are a number of different schools of thought about when to divulge. Too soon and too blatantly and you will scare off a woman who could have been convinced. If you check out this article, "Convincing Her to Try It" it will give you an idea of the factors involved as far as women are concerned...and there are many. (Myself I divulge right on my profile on FetLife because not only is pegging my passion, I write about it and teach about it, which presents additional challenges.) For men there are pitifully few women who already love pegging or are turned on by the idea of it, so limiting yourself to searching only for women like that would narrow your choices ridiculously. So you find a woman you like to date and when do you tell her, right?

Your generation tends to be much more open minded about sex and accepting of what my generation would deem as quite kinky stuff. So you could divulge early and first say you are really into ass play just to see if that is a hard limit for her. Asses can be a very hard limit for people of all ages because of the whole excrement factor. Usually a woman who is into receiving ass play is more open to her guy suggesting that it be his ass they play with. Sadly, even women your age sometimes have the He's Gay reaction. If you can get them past that they usually discover pegging rocks. Don't wait too long, though. Dangerous to wait too long because then you are emotionally involved and she might say absolutely not.

Another option is to do what this man did: "Vanilla to Pegger - One Man's Story". I could talk a long time about this subject - it is a major topic of discussion everywhere people are talking about pegging. I do wish I had a magic wand to instantly make a woman interested in strap-on sex. But I guess the whole dance is an important and necessary step in developing more intimacy and opening to each other.

I went back to my sensual massage therapist today for a 1.5 hour session, I wish I had a mindblowing experience to report back to you guys, but it was another good, but not great session.

So I get there and just like last time we take a minute or two to plan out what we're gonna do. Last time I thought the sensual massage she gave was amazing, she does a more traditional massage for a bit, then with me laying on my stomach, she focuses in on my erogenous zones. If you've never had this done, it just feels incredible. She runs her fingertips all over my butt cheeks, all over my taint, asshole (but no penetration just yet), balls, and just the right amount of contact with my cock. This went on for about 25 minutes and I had told that I wanted her to go straight into a prostate massage right away while I was charged up from the massage.

Part of the problem was that she doesn't really have enough toys. I was hoping she had kind of a handheld prostate massager or vibrating dildo or something to use on me while I was laying on my stomach, but she did not. Anyway, she went into a prostate massage with her fingers for a little bit and it was ok, but I guess my prostate wasn't quite awakened yet b/c it didn't really start any intense pleasure waves.

She had mentioned last time that she got really sore from fucking me in the same position for too long, so she asked me to turn over onto my back and I was ok with it b/c the manual prostate massage was getting a bit stale. She used the same strapon as last time which was a bit of a letdown, I was really hoping she had a vibrating one and was a bit surprised that she didn't. Just like last time it felt pretty good, but not great. I was getting erections every now and then as well so I think I was a bit more relaxed than last time, but still not close to any kind of orgasms. Part of the problem may have been that the strapon she uses is kind of a beginner one, it's a bit less girthy than I'd like, and it isn't that long, so when I'm on my back we both have to strain a bit too much to get it deep enough to hit my spot, which dampens the mood a bit.

So then she asks me to turn over again and I was thinking cool I can relax on my stomach while she goes to town on me, but instead she suggested a doggy style position with me on all 4s and I agreed. The odd thing about this position is that it almost led to too much penetration, I think the strapon was pounding me a bit too hard, but it still felt pretty good, and finally in this position I was getting close to mini Os, but couldn't quite get there. This was also a completely different sensation of being penetrated than while on my back. I don't know exactly how to describe it, but it's a more raw and pounding feel. It was definitely a bit different and was the first time I got the sensation where I need to take a #2. It seems like this is probably not a position you want to try right away if you're new to pegging. This position is ok for 5-10 minutes, but after awhile my shoulders just got really tired b/c they were supporting most of my weight and some of hers. At this point there was about 15 minutes left so I ask her if I can get back on my back so she can finish me off.

It is kind off odd that I was pretty erect during the prostate massage, got a couple hard erection the first time I was on my back (none during doggy though), but once again I had trouble getting an erection the second time on my back. She wasn't really pounding me that hard with the strapon, I think it might just be a little too difficult to hit the right spot without us both doing acrobatics. Anyway, I really had to focus a lot to finally ejaculate, she was telling me stories of her lesbian exploits in strip clubs and such, I'm not sure if they were true or she was embellishing a bit for my benefit, but I shut my eyes and really focused in and had a pretty good ejaculatory orgasm. It seemed like semen was shooting everywhere and some even shut up to my cheek bone, which she found quite amusing, I thought it was pretty cool too and I didn't mind a bit of laughter at my expense b/c I believe the sexual arena is a place to have fun and not take yourselves seriously.

Overall, I would have to say the experience was maybe slightly worse than last time which was a bit of a disappointment. This one was 90 minutes instead of 60, so it was a bit more pricy at $165 USD. I'm not really certain if I want to do another session or not. I think if I do I will probably wait 6 weeks or so. I really wish she had a vibrating strapon b/c I think that would make a world of difference (I love my Aneros Vice). As such, I'm not sure if I can really justify the expenditure. The sessions are not even in the same ballpark of pleasure as some of my better Aneros ones, but there is definitely something to be said about experiencing this pleasure completely at the mercy of another. I can only imagine how great it might be to share it with someone you truly love. Another part of the problem is that when I'm really trying to focus on the sensations around my prostate to build them up into an orgasm, I am pretty quite and focused, but I think this might confuse her and make her think I'm not enjoying something when that couldn't be farther from the truth. It is a bit hard for me to stay completely focused when I have to balance my pleasure with also providing her feedback.

I've started dating 2 girls so hopefully one of these relationships blossoms into sex and I will for sure try to introduce pegging into any new sexual relationship. I guess the dream of being fucked by a Feeldoe (or its equivalent) will have to wait a little longer.

Rando - I love the way you are so generous with sharing the details of your experiences with us. Thanks for that.

The sessions are not even in the same ballpark of pleasure as some of my better Aneros ones, but there is definitely something to be said about experiencing this pleasure completely at the mercy of another. I can only imagine how great it might be to share it with someone you truly love. Another part of the problem is that when I'm really trying to focus on the sensations around my prostate to build them up into an orgasm, I am pretty quite and focused, but I think this might confuse her and make her think I'm not enjoying something when that couldn't be farther from the truth. It is a bit hard for me to stay completely focused when I have to balance my pleasure with also providing her feedback.

Yes - I would have to say that some of my masturbatory experiences that involve the G-spot are far more intense than what I can achieve with a partner, but for me having the partner there is still preferable most of the time because of the human connection factor. I wish you the best with your blossoming relationships!

@ All -I found a great description by a man about the first time his wife did any serious anal play with him with a toy. Not quite pegging, but well written, humorous and encompasses everything from preparation to play. Enjoy.

Great read Ruby!I was extremely concerned about the pineapple under the heading "Tools and Toys I used", Those leaves on the top are very sharp, not to mention the girth of the actual fruit.I needn't have worried, although I thought that use of pineapple was very considerate of him!

Rando;Thanks for the excellent and comprehensive report. Considering that you're paying what would be top dollar in my neck of the woods, you should get complete satisfaction, your way; vibe, positions, whatever it takes. I'll bet it works out better for you when you have a GF who is into it. Best of luck in finding one.

Ruby;Thanks for the link. BTW, I subscribed to your stories and recommend them to anyone into this kinky side stream activity.

Skywalker;So, you chickened out of the Share XL, didn't you? :)

Sensitive;Many independent massage therapists will do prostate massage, toys or strap-ons. Find them on Craigslist or Myredbook or in the local street newspaper's back pages. The code word is "FBSM," full body sensual massage. Then, ask the lady if she does what you want.

sensitiveguy22 - that was a great read - only part that made me blanche (though I know it was meant to be humorous) was:

5. Have the girl clip her fingernails. Maybe decades from now, sticking sharp objects up your ass will be the hot new thing but that’s a different article for a different generation.

No - that will never be the hot new thing. Ever!airbag - "double perversion"? If perversion means totally hot, yes. That position allows for a lot of intimacy, eye contact, kissing. You just have to be careful that the family jewels don't hang down in the way and get knocked around. That is why you see men holding their balls up sometimes in gay porn. Not always necessary depending on the angle and how everything hangs, so to speak.

Is this more or less what it meant by "woman on top/reverse missionary"?

That's from Tristan Taormino's Guide to Anal Pleasure for Men, which I was just watching and thought that position was super hot as opposed to others where your back is to the girl and you can't see her or anything.

[QUOTE=sensitiveguy22;101729]Is this more or less what it meant by "woman on top/reverse missionary"?

I think so sensitiveguy, now just imagine her leaning forward all the way to passionately kiss you and putting her weight on you (watch out for your balls though! those boys can get squashed) Now bring your legs up onto her bottom or lower back and push her in, as if she needs any encouragement! Very passionate.

Yes Ten_s_nut, I have chickened out for now, the standard Share has had a run since, but you now how it is, it's hard to stop to change equipment!